A Sexual Awakening

Story Info
James knows his mom's secrets.
15.2k words
4.38
128.5k
95

Part 1 of the 6 part series

Updated 06/07/2023
Created 04/22/2015
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
twofourthree
twofourthree
1,680 Followers

I am not a writer, far from it. Except for the names and places, the stories you read are for the most part true. Still they are not biographies. Artistic license has been taken to enhance or in some cases minimize the events described. All sexual situations were between consensual adults within the framework of their story.

This is the fifth of the ten interviews I have worked on over the last three years.

Most of these stories cover several years. I will try to keep the chapters short. I suggest you save one for reference. None of the stories are mine, any personal friend, or relative.

Janice told me her story over the course of a week. It is about her sexual awakening and the person that brought it all about.

*****

Damn I wish I wouldn't have worn these heels today! I admonished myself as I teetered on them. How was I to know he would do what he did? Still I had bigger problems to worry about. The discomfort in my calves and thighs wasn't anything compared to the throbbing in my ass and the dull ache in my nipples. Glad I wore my long flowing summer dress to work today. At least this way my pussy and ass are hidden. Still my tits would be clearly on display should someone come in his office.

"AAhhh." I groaned as he pulled the string attached to my nipple clamps.

"Fifteen more minutes slut!" He whispered in my ear. I could feel his hot breath sear my cheek. My pussy dripped even more. This isn't how I envisioned this happening. Oh I wanted him. There was no denying that but not like this! In my dreams we would start as lovers. Only then would he learn my deepest desires. But this...this is so sudden. I reminded myself to take long deep breaths. Stay focused. Enjoy the moment before moving to the next.

I could feel the saliva drip down my chin between my aching tits. I tried to control it but the ball gag was too big. I never thought about that when I bought it. I wasn't sure if not being able to see the clock was a good thing or bad. All I know is this was bordering on torture. Not real torture of course. Just the kind of titillation I dreamed about! The kind he found on my computer. Well the companies computer to be honest.

I wondered then if he saw all of it. Maybe that is why he moved her right across from my desk. She is so young but God is she beautiful. It had to be what he found on the computer. How else would he know I fantasized about being tied up? How else would he know to tease me with her day in and day out?

If I tried to stand the tension on my nipples would be relieved but the plug halfway in my ass would pull free. If I plunged the dildo deep in my ass like I wanted to the weight of my tits would all but rip my nipples off! He made that clear that I wasn't to let my ass do either of those until my lunch break was over.

The single smack he administered to my ass was enough to convince me ten more would be delivered if I failed. My legs were going numb. I was almost resigned to the fact I wouldn't sit for the rest of the afternoon when he pulled on the string again.

"Five minutes. You are almost there!" He brushed my ear lobe as he spoke. Chills went down my back.

I felt his hand caress each tit. He gently tease each thick nipple. The numbness turned to exquisite pain for just a second. His hand felt odd. Like he was wearing a glove of some sort. Moving lower his hand moved under my dress. He rubbed my clit then found what he was looking for. He found my pussy lips hanging down. I knew they did. Thick and meaty they were my worst asset at least according to my ex-husband. My boss gripped them tugging lightly on them. Slippery with my oily juices they slipped through his fingers. It was all I could do not to ram the plug all the way in my ass.

"One last test my slut. Pass this and you will be spared. Fail and you will be mine. It's up to you!" He nipped my earlobe. "Remember no cumming!"

God what have I gotten myself into I thought. So many conflicts. How did he know what buttons to push? Why was he so good? Was this all just chance or did my earlier efforts work? I was like butter in his hands and yet we had never so much as kissed on the lips before.

Sure he saw the goods a time or two but that was years ago. But this? My darkest secrets how else could he have known? Was I that indiscreet? Regardless I was here now, and so was he. Did he have me right where he wanted me or did I have right where I wanted him? It had to be the first. I couldn't admit it was the second. Not for now anyway.

He slipped something deep inside my pussy. The pressure intensified in my ass. Oh god no not that! Then I felt him turn it on. Oh shit! Did I really want this? My brain said no. My body screamed yes! He played with me for the next few minutes bringing me to the edge. Then taking pity he turning it off.

He was so good at this it could have been me at the controls. Many times I would sit in the chair outside this office and pleasure myself with this very vibrating egg. Sure I dreamed this day would come but not here and definitely not with him. Did she do this? No, I couldn't believe that. We worked together but I always hid my feelings for her. Who else knew? I tried to think. Just then he turned it back on.

"AAGGGHHHH! My whole body shook. A large quantity of drool flowed over my lip down my chin. I could hear my pussy dripping on the new hardwood floor he just had put in. I couldn't figure out why he wanted the wood until I heard the clickity clack of my heels walk across the office to his desk.

Had it really been almost two weeks? Each day since he showed up he gave me a look that let me know he knew something. But I was too excited to realize what that would be. Too distracted in my fantasies to notice. That is until this morning. When he told me to come into his office for lunch, I never thought this is what he would make me do. Or was he letting me do this to myself?

It all became so blurred. He never actually touched me, except to tie my hands behind my back. The rest I did myself. But he did insist I do it. He even made me unlock my desk and bring all of these things in here so I could do as he instructed. Still the way he said it. The softness and then the clear commands. They were so...so... perfect.

Now I am here in the position he devised and I facilitated. The implications were clear from the start. Nothing was left to interpretation. Nothing left to debate. He made it clear where he stood. That alone was enticing. In the end the final decision was mine. It has been almost thirty minutes. Thirty minutes! The most incredible thirty minutes of my life. This would have all been so easy under different circumstances. But why now. Why here. What about her. And why him? Do I really want this is or it just one of my many fantasies?

"Two more minutes!" He whispered. He turned the vibrator off in my pussy. I could do this I thought. I can hold off this long. I had done it numerous times to myself. Ten minutes may be a stretch. Five for sure. But two? That was a piece of cake. Then he did something that I couldn't have foreseen. Next to my clit my nipples were my most sensitive body part.

I felt the clamps on my nipples release. Blood rushed back to parts of my tits that should have never been cut off. He immediately caressed each tit increasing the warm throbbing in my nipples. His tongue tease the rubbery nubs then sucked each one. If it weren't for the fact he turned off the vibrator I would have cum instantly. Still I was confident. My fate was in my hands. He removed the gag from my mouth.

Then he kissed me. Oh my god did he kiss me! I never thought it would be like this. He removed my blindfold the sunlight streaming into his office hurt my eyes.

"One minute!" He reached around me. My hands secured at the wrists. My fingertips helping me to steady myself. The dildo still just partially in my ass. I could do this! I was home free! One more minute and this would all be over. A wonderful memory, but just that a memory. He placed the control to the vibrator in one hand. He looked at me as I gave him a questioned look.

"I told you it would be up to you! Choose wisely. Your decision is final." He reminded me of the conversation we had before this all started. I believed him then and I believe him now. Master stood and walked to the door letting me know he wouldn't influence this in any way.

"Thirty seconds!" He called out. He had an impartial glare on his face. Was he really that cold? Or was he doing that for me. I needed to know, but there was no more time. Twenty nine and a half minutes wasn't allot of time to determine the rest of your life but here I was. I had put myself in this position and I could get myself out of it. If I wanted to.

I didn't. I wanted in. I knew long before this moment what I wanted. What I didn't know is if he would be the person to do it with. He proved to me during the last week I could trust him. He proved today he could he could be firm but loving. He wasn't only my first choice, but I knew he was the best choice. I turned the vibrator in my pussy on full speed. Nanoseconds later I sat down forcing the widest part of the butt plug past my greedy sphincter. My pussy spread the cold juices I had leaked on the floor as my lips splayed flat.

The orgasm I was having was so intense I tried to expel the egg from my cunt! It just vibrated against the hard floor and abused my clit further. I wish he had left the gag in. I needed to scream. I needed to release some of this glorious feeling as it ripped through my body. My legs were of no use. I dropped the remote as I fell to the side. Fortunately egg fell from my cunt and was now bouncing wildly on the floor. I was in a fetal position my legs clamped tight, the plug now secure in my ass. Wave after delicious wave of ecstasy left me a twitching mess on the floor unable to move.

He came and turned off the egg leaving it lying on the floor. He released my wrists, knowing I was too weak to now do it myself.

"Slut you need to clean this floor up!" I reveled as he called me that name again. I was. And now I was his. I reached for the hem of my dress. "NO! You will use your mouth!" He commanded.

I hesitated but his glare let me know the training was now in session. I turned and with what little strength I had started to lick the floor clean. I had tasted remnants of my pussy before but this was pure cunt juice. It was disgusting and yet so erotic. He knew how to play me. He moved closer. Lifting the hem of my dress he flung it over my back exposing my ass and pussy. Taking three fingers he jammed them deep in my cunt. I let out a groan. My face turned to the side mashing on the floor as I tried to raise my ass higher so he could finger me. My tender tits mopped the floor of my cum and spit.

"Lick!" He demanded. I started cleaning the floor again. Occasionally licking the top of my breast as it swung near my tongue. He pulled the slippery plug from my ass and worked in tandem with my pussy. The feeling was too much. I had held off for so long before that now I couldn't hold off at all.

"Please master!" I begged. He didn't make me beg again.

"If you truly want to be my slut come for me now!" He commanded. I couldn't have stopped if I wanted to. I was his. I wanted this. I needed this!

"Thank you Master!" He slammed the plug deep in my ass. My cunt clamped down on his fingers. How I didn't explode I don't know. But that wonderful feeling of being overtaken with bliss surged through me once again. He continued to fuck me with his fingers until I gripped his wrist with both hands and pulled him free of my pussy.

"Let go!" He demanded. I did as instructed. He rolled me on my back splayed my legs exposing my hairy pussy. He smacked my pussy with his latex gloved hand my clit and pussy lips bearing the stinging attacks. I was going to try and stop him but this must be my first lesson. "I decide when you have had enough! Now get this place cleaned up and get back to work. Your break was over minutes ago."

"Yes Master."

"James." He corrected me. "When we are in the office you will call me by my name. In the house it will be Master. In public Jim will do."

"Yes James. I understand." I looked at the floor one last time. He threw hand towels for me to dry any wetness. I stood up. I placed my tits back in my bra and then pulled the dress back in place. I was looking for my panties.

"You will not wear them in the office when I am here. He showed me he had them. You will leave that plug in your ass until I tell you otherwise."

"Yes James. Will that be all?" I asked looking at him knowing the rest of my life was about to change.

"I have some calls to make. I will get back to you later." He replied in a businesslike manner.

"May I have my panties back for now?" He looked at me surprised I would be so brazen to ask.

A smile crossed his face. I think he liked a woman with a bit of spunk. Submissive but sassy. He opened the drawer and tossed me the panties. I pulled up the hem of my dress and started to stuff the material in my pussy. When the last of it disappeared I looked at his slacks. A massive bulge let me know I had his attention. "I don't want to soil the company's furniture."

I was just about to close the door.

"Mom! I like my women with shaved pussies. Waxed would be better still." James explained.

"Janice." I corrected him. "When we are in the office you will call me by my name. In the house it will be Mom or slut or whatever you wish. In public Jan will do." I repeated his words. "I have a razor at home you can use!"

I closed the door before he could respond but I was pleased to see he was still smiling.

"Janice. We will be leaving at two. Mandy do you think you can hold the fort down for a couple of hours?" He looked to the young secretary across from me.

"Yes Mr. Redman." She replied. Mandy gave me a seductive smile.

"Thank you Mandy. Janice and I are going to the hospital. I should be back before you go. Call me if you need me." James was so nice to her.

He went back in the office. I could see him keep an eye on me. Maybe he was planning our next meeting.

At two he pulled on his suit coat and stood in front of my desk.

"Shall we?" He took my hand Mandy smiled at me again. Leading me to the elevator we stepped inside. I was expecting some advance but he just held my hand. The doors opened and he led me to his car. It was a convertible. The top was down the brown leather interior baking in the sun. Jim opened the door. I started to sit. "Your dress!"

"Sorry?" I wasn't sure what he was talking about.

"Lift up your dress. I want your bare ass on that leather!" Surely he was joking. I looked at him. He wasn't. I flipped the back of my dress up and sat down on the seat. The hot leather smoldered my ass.

"That is your first punishment."

I wasn't sure for what. I could have done so many things wrong. I wiggled in the seat the butt plug drove deep as the padding formed to my ass. We stopped to eat. I was famished and so was he. I lifted the back of my dress as I slid in the booth. Anyone watching would have gotten a clear view of my ass. He seemed pleased.

Jim ordered for us both. The waitress seemed somewhat taken back by his boldness.

"So, you have seen the books what do you think?" I was startled he wanted to talk business at lunch.

"I am no accountant but they don't look good." I straightened up a bit thrilled to know he valued my opinion.

"Too much debt. Janice this is a house of cards. He is on the brink of losing everything!" James wasn't happy.

"There must be some money someplace. He keeps spending it!" I added.

"Well he is either a very smart man or a very stupid one. If he has money hidden it isn't in the business."

We ate lunch, rarely talking except about the business. James paid then told me to head to the ladies room. I did he went with me locking the door.

"Bend over slut. Face away from me." He put one foot in front of the door. I backed up to him he lifted my dress. "We need to get this out of you it has been in long enough."

Jim gripped the butt plug and slowly pulled it from my ass. He stroked it in and out a few times then pulled it free. I stayed bent over. He could see my puckered hole slowly close up. He looked at the plastic toy.

"You weren't prepared?" He asked.

"I didn't know!" I explained.

"Now you do. Go clean your ass up then let me inspect it before you set in my car."

I took some paper towels and dampened them. Moving to a stall I used tissue and the towels to wash and dry my asshole. I returned to find James had washed the butt plug and then wrapped it in towels. I turned and offered my ass for inspection.

"That will do. I suggest you keep wet towelettes in your purse."

"Yes Master."

We exited the bathroom just as another patron wanted to go in. She gave Jim a nasty look. My ass burned a second time as he helped me in back in the car. My pussy was starting to saturate the panties stuffed up it from before.

We took the elevator to the intensive care floor. We passed the nurses stand and headed to his room. We passed the waiting room. 'She' was there. I saw her head in my direction but when she saw Jim she stopped. Jim walked right in the room like he was a doctor. The nurse gave him one look then stepped aside. Last week they tried to throw him out. Tried is the key word.

"How is he doing?" Jim asked genuinely concerned.

"No change Mr. Redman." She answered.

"Is there hope?"

"There is always hope sir."

"So you're saying he will pull through?" We all knew she couldn't answer that.

"Let me call the doctor Mr. Redman."

"Thank you that will not be necessary. My apologies for putting you on the spot. That was rude of me." James offered.

"That's ok sir. We are all concerned." Jim moved next to her. He kissed her on the cheek. The young woman blushed. At that moment I knew how she felt.

"You are too kind. Thank you for caring." Jim started walking out leaving me standing with the nurse. We exchanged awkward glances. "Mother we have taken up enough of her time." He then said.

I looked one last time at my ex-husband Harold. He looked so peaceful. Taking my hand I joined James as he walked down the hall to the waiting room. Latisha saw him coming. I could see her step back to her son looking for support.

"Latisha! How are you?" James moved closer to her. She was up against her son when Jim kissed her cheek.

"Why do you do that?" She asked. "I have told you to call me Tess like everyone else."

"Well I am not anyone else. I am your stepson. I think a light kiss on the cheek isn't only warranted but shows love and sincerity!" I almost laughed but knew better.

"What do you want 'stepson'? You got what you wanted. The company is yours!" Her son replied clearly upset.

"Not really. Not as long as he is alive. I am just running it for now. But technically, only until he dies or is deemed incapacitated with no reasonable chance of recovery. Dad is still in charge.

That brings me to the point I wish to make. The company is all but insolvent at this moment. Yes we can struggle along for some time maybe years. But you see he hasn't been drawing a paycheck for some time. That means you Latisha will not be getting paid!"

"What!" She screamed. "I knew you were out to screw me!"

"Mom! You are in a hospital for god sake. Stop yelling." Her son tried to calm her down.

"I figured you would say that but not true. Look if you know where he is getting the money to live on I will assure you, you will get your share. But since you no longer work for the company and he is not on the payroll my hands are tied. I am bound by the court to run this company as fiscally responsibly as possible."

James looked to her son. He is slender medium height and smart. Clean cut well dressed. He always dresses sharp. Like Tess he is African American.

twofourthree
twofourthree
1,680 Followers